On this day, 6 years ago . . . (Happy birthday to Permission To Screw Up!)
Six years ago today (October 10th), Permission To Screw Up made its debut. Six years! I can hardly believe it.
I haven’t always done the best job of honoring the book and what it’s meant to me, to our team, and to so many people across the world. It’s such a huge part of our journey, and it represents so many lessons learned. So today, on its sixth birthday, I want to take the time to honor Permission To Screw Up by sharing with you six memories and behind-the-scenes moments that really stand out to me . . .
The Gainesville book launch. A couple days before the official publication date, we hosted a soft launch in Gainesville, Florida, which is where Student Maid was headquartered. The most amazing group of people showed up: friends, spouses, families, and so many people from the local community who supported Student Maid for so many years. One of my friends drove two hours with her newborn to be with us. A few of my professors from the University of Florida were there, as well as some of our very first clients and team members who had graduated and moved away. My parents and the parents of some of our team members were there, and we even had our Student Maid DJ playing music. It was so special that we got to celebrate this huge moment with them first, and I'm really grateful that our publisher allowed us to give them all copies of the book a few days early. It meant a lot to host this event in the place where the Student Maid story began—almost literally: The restaurant where we had the book launch party was the same one where I spent $1,000 of my $10,000 business loan on sushi and sake bombs! (If you don't know what I'm talking about, check out Chapter 2!)
Choosing the title. When we started talking about what would make a good title, our publisher and agent told me about the “dinner party test”: You should be able to say the title and subtitle at a dinner party, and everyone should understand what the book is about. But it’s really hard to do that! Simon Sinek is the one who suggested “Permission To Screw Up.” At the time, I didn't love it, but I agreed that it could be a placeholder while I tried to come up with other titles. For a time, I thought we might go with “Hot Mess,” but looking back, I am so glad we decided not to call it that. Around this time, I went to Seth Godin’s house for dinner, and when I told him I was struggling with the title, he went off and brainstormed for like five minutes. He came back to the table with “Shameless Leadership: Care Enough to Fail.” I loved it—especially the subtitle—but I still felt more drawn to “Permission To Screw Up.” I also brainstormed with my then-boyfriend (now husband!) Spiros. We tried a technique that I had just learned about where you get a bunch of Post-It notes, set a timer, and write down as many potential titles you can think of—one on each Post-It—before the timer goes off. Spiros (who is a surgeon and has a science brain) suggested titles like, “How To Improve Your Culture,” and “A Book About Culture.” I came up with things like, “Shoulder to Shoulder” and “Lead with Your Heart.” It was so funny to see the differences, and I still laugh about that brainstorming session to this day. It meant so much to me that he wanted to help me, but I told him he should probably stick to being a surgeon. Now, I can’t imagine calling this book anything other than Permission To Screw Up.
Choosing the cover. This was one of the most challenging parts of the whole process. The marketing team wanted a picture of me on the cover, but I didn't want that at all. I thought it put too much of the focus on me. I also worried that years down the line, I might not like the picture anymore, and I’d be stuck with it. Looking back, I'm not sure if I made the right choice or not, but I know that choosing the cover was an equally frustrating process for me and for our publisher. Their amazing art department worked on so many different covers, and they just didn't resonate with me. I remember that at one point, Monique (our Chief of Growth) and I flew to New York to see the potential cover designs in person and try to choose one. We were in a conference room, and they had laid out hundreds of covers on this huge table. I didn't like any of them. The cover of the book is so important, and I wanted to love it. It’s not that the publisher didn't work hard and produce great ideas, it's just that none of them really stood out to me as “the one.” It wasn’t until the very last moment—the last day I had to think about it—that they sent over a version of the cover you see today. When I saw it, I just knew that that was it. I loved it. After that, we sent the art department flowers two weeks in a row to thank them for their patience and hard work.
Ice cream sandwich day. The day the manuscript was due, I hadn’t slept for more than 24 hours. Rachel, our Chief of Content who wrote a lot of the book with me, flew to Gainesville to be with me for the final push, and she stayed at my house for a week. My mom was there, too, helping us stay fed and making sure we had clean clothes and editing occasionally. Most nights, Rachel stayed up and worked with me until the wee hours of the morning, but that day, neither of us had gone to bed. What I remember most about the end of that time together was writing the last chapter of the book (the famous Chapter 7). When it was finally done, all I wanted was an ice cream sandwich. It was 8 in the morning, and there I was on the couch, in my PJs, under a blanket, hair a mess and huge, dark circles under my eyes, eating this ice cream sandwich. Rachel took this picture of me, and I think it represents what it feels like to write a book pretty well: There are so many high moments, but there are some pretty big low moments, too. When I see that picture now, it brings back memories of what it took to get that book out into the world. I won’t put myself through anything like that the next time around because I’m so much more mindful of my health now (I ended up giving myself a kidney infection because of the stress and lack of sleep. Yikes.). At the same time, I know that writing a book is a lot of work, no matter how you approach it. There will always be moments where you have to push through and keep your foot on the gas. Ice cream sandwich day represents all of that to me.
Dedicating the book to my sister. Almost from the start, I knew I wanted to dedicate the book to my sister, Lauren. She's always been my biggest fan, and she also supported me so much through the whole book-writing process. She flew to Houston and stayed with me for weeks on end when I was really struggling with writer’s block. I called her my book babysitter. She held me accountable to writing. She was there to be a listening ear. She made countless edits. She would read something and tell me if it sounded authentic, and she encouraged me to stay true to me. My intention was that she wouldn't find out about the dedication until the book actually came out and she was holding it in her hands. But a couple months before the book launch, I went to New York to record the audio version of the book. Lauren lives there, so she came with me to the studio. I didn't think about the fact that I would be reading the whole book, including the dedication, for the recording. She was standing right there next to me when I read it—so that’s how she found out. I don’t regret it, though. She was still so surprised, and it’s such a special memory to me.
Launching the book in New York. We flew the whole leadership team to New York to celebrate the official launch of the book. We had a special event on publication day at NeueHouse, a unique coworking space in the city. Simon Sinek, who wrote the foreword, interviewed me about Permission To Screw Up in front of a live audience. So many people were there. When I looked out into the audience, I saw my amazing team, many New York-based friends, some of our first interns, and even my college roommate. It was such a surreal moment. It felt like this was the start of something big. It felt bigger than us. After the book launch event, we went out to a nightclub and invited everybody on the publishing team, including our editor. It was so much fun—dancing the night away and celebrating launching Permission To Screw Up into the world. The most special part of that New York trip was having the team there with me. That was the biggest thing we had ever done together up to that point, and we stayed in the city for a few days to celebrate this huge moment in our journey.
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It’s been so fun to reminisce on the launch of Permission To Screw Up. Thinking through these memories makes me realize even more that we made the right choice to pause the second book. Though there were plenty of lows and challenges with writing the first book, it felt right. I knew that I was writing the book that I was meant to be writing. I want to feel like that again when I write the second book. I know that that day will come, and when it does, it will be so special.
By the way: Did you know that we have a Permission To Screw Up discussion guide? We created it to help you dive deeper into its themes, learn how to give yourself permission to screw up, and create a culture that empowers people to be human, mistakes and all. The discussion guide is pay-what-you-can because we never want the fee to be a barrier.
So with that: Happy anniversary, Permission To Screw Up! Thanks for all the memories and for everything that you've taught me about myself and about leadership. And thank you to everyone who has reached out over the years to tell us how much you love it. It means the world to us, and we’re so happy to share this journey with you.
Big hugs,
